My First Time with a Man (MTF)

*** This is the first story that I've ever written like this, so please go easy on me. ***

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I had been waiting for the perfect time to take it a step further with a twink that I had gotten to know over the Internet. I am attracted to the twink-type because I'm not a fan of body hair. I shave my own body year round. Ryan lives fairly close by, but my wife hasn't been out of town without me for awhile and we had never gotten together. This past October, she needed to take a trip to get some training for work and I saw the perfect opportunity.

I had the house to myself for a few days and let Ryan, my online-only boyfriend, know that I wanted to see him. He told me that he could come over that same night so I decided to take a nice, hot bath and get ready for him. But, before hopping in to the tub, I laid out an outfit that I thought Ryan would like that included a pair of black, thigh-highs, silky, black panties, bra and a gray dress. Now that my bath was ready, I slipped in and took care of shaving my body nice and smooth. It feels so good to slide wet, freshly shaven legs together. It feels even nicer, though, to slide them in to a pair of stockings or pantyhose.

Once I had finished in the tub and dried myself off, I slipped in to my bra and panties. I have to stuff my bra with pantyhose though to look somewhat convincing. Before slipping in to my stockings, I decided to paint my toe nails a dark red and put my toe ring back on. I knew that they'd look nice underneath my stockings. I also painted my finger nails the same color and let them all dry. I applied some light eyeliner and red lipstick to top things off. I am no expert in putting on makeup, but it really felt nice to look feminine. I then sat down to slide in to my black stockings. I was right. My toes looked really nice.

I knew that Ryan was arriving soon and this was our first time getting together. In fact, this was my first time with another man and my cock was already dripping pre-cum that I needed to take care of. I put on my dress and finished off my look by putting on my brunette wig. While brushing my hair and looking in the mirror, I realized that I definitely did not look like a man. I looked and felt like a woman who was anxiously awaiting her first night with a man.

The doorbell rang, so I slipped in to my three inch heels and made my way to the door. Since I'd worn heels in private for many years, I had no trouble getting to the door. It was so nice to be able to feel my legs rubbing together and to hear my heels hitting the floor. I peeked out of the window to make sure that it was Ryan and, then, opened the door.

Ryan gave me a quick look up and down and smiled as he walked in. I gave Ryan a quick look up and down also. He looked nice. Ryan was really a cute guy, with a tight body. He was wearing jeans and a dark T-shirt. His muscles were obvious and seeing him caused me to become excited. He gave me a hug and a kiss that lasted more than a few seconds. It was really pleasurable to feel his lips and the warmth of his body so close. This was a first for me and I couldn't believe this was finally happening.

I walked with Ryan in to the living room and we sat down to watch TV. But, television was the furthest thing from our minds. Ryan put his hand on my stocking-clad thigh and leaned in for a kiss. My heart was racing and I felt a little nervous, but I wanted to taste him. I kissed him back and while leaning in, he slide his hands up my dress to feel my silky underwear and my hardening cock. At the same time, I reached over to Ryan's crotch to feel his cock through his jeans. It was definitely hard.

This was another first from me. I couldn't believe that I was taking it this far. No one other than my wife had seen me dressed in women's clothes. Now, I was showing another male what I looked like, and I was actually touching his body and dick. Never in my wildest dreams did I imagine this happening for real. My wife knew that I was bisexual, but she didn't know that I was planning this night in my mind every time that I masturbated.

As we continued to kiss and feel each other, I unbuckled his pants to pull his jeans down and he finished taking them and his shoes off. I couldn't wait to see his dick and pulled his underwear down. His dick popped out and I could tell that he was well groomed and cut. It looked delicious. I definitely prefer a circumcised dick. Ryan's was the perfect size, not too large and not too small. I was going to be able to take it inside me and couldn't wait.

Ryan stopped kissing me and I leaned over and licked the tip of his penis like an ice cream cone. Ryan moaned and told me to go for it. So, I took the entire penis in to my mouth without hesitation. It felt so nice to hear my man moan as I licked and sucked his manhood. While I sucked, I pressed down on his taint where his prostate was located. I knew that would add to his pleasure. I fondled his hairless balls and nearly lost it myself as I sucked on him. I loved the sight of my hair dangling over his body while I sucked him. I could feel my own dick stiffen inside my panties.

I didn't want him to cum though because I wanted to ride him like a cow-girl later. So, I took Ryan to the edge before sliding over and lifting up my dress to pull off my panties. I slid them down my legs and over my heels. Ryan grabbed them from me and sniffed them. I know that he'd probably notice that they were a little bit wet and that turned me on even more. He actually licked the little spot of pre-cum that I left in panties. While I was getting situated I could see his dick pulsing as it waited for more attention from me.

I didn't worry about a condom because I wanted Ryan's cum inside me. I wanted to know if I would be able to feel his dick pulse as it ejected his cum inside me. I wanted to have it leak out of me in to my panties. So, I grabbed some lube and moistened my hole and lowered myself on to Ryan's dick. Since I've practiced for years with a similar sized dildo, this was no trouble and Ryan smiled and leaned back as I slid down his pole with ease. I cannot describe the pure joy that I felt as I was filled with his manhood. I straddled him with my stockinged legs on the outside of his legs as he sat on the couch.

With his penis still inside me, I wanted to feel Ryan's entire body so I slipped his shirt over his head and leaned in to feel his warmth. It was really nice to feel his arms wrap around me and to comfort me. He touched the back of my head and pulled me in for a passionate kiss. My mind was racing knowing that I was sitting on my couch with my boyfriend and we were having real sex.

After breaking away from our kiss, I began to slowly move my body up and down on his dick while looking in to his eyes. We kept our eyes interlocked while I rode him. I could feel his member inside me as it filled me up and then I lifted up only to take him in again all the way. My dick was still hard, but flopping on his stomach as I kept riding him. I liked the way that the bottom of my dress felt on my body and partially covered my stockinged legs and Ryan's body. Ryan kept his hands on my waist and I reached behind and underneath me to feel the base of his dick as it entered me. I cannot describe the ecstasy that I was in. I was finally feeling, at least partially, what a women feels like when taking her man and I loved it.

Ryan and I continued to kiss and fuck for nearly fifteen minutes before I could feel his body and dick tense up. I kept on riding while he moaned and shot his load inside me. I could feel his dick pulse each time that he spurted another load inside me. And, at the same time, this feeling and the knowledge that I made my man cum brought me to orgasm right on to his stomach. This was the third time that I've cum without touching my own penis. But, the first with a dick inside me.

Ryan was leaning back with a huge smile on his face. I kissed him and told him that he was mine and I was his.

I lifted my dress up so that I wouldn't get cum on it. I wanted to feel our bodies together with my warm cum squishing between us and his warm cum leaking out on to his dick. We kissed again and Ryan told me that next time we would have to try the missionary position in his bed. I told him that there were many more positions to try.

I slid off his dick quickly and we went to the bathroom to clean ourselves up. I slipped on my panties and found out what it must be like for women as their man's cum leaks out. My panties were wet. It's a good thing that I have a drawer full of panties. Hmmm...maybe Ryan can borrow a pair for next time.